Potassium Carbonate → 2-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzaldehyde

HRID 537603Notes

Reaction equation

HRID 537603 reaction equation
[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:31]=1)[CH2:27]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O[C:56]1[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:57]=1[CH:58]=[O:59].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH:31]=1)[CH2:27][C:56]1[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:57]=1[CH:58]=[O:59])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 672488813,5-Di(docosyloxy)benzylchloride

Product 1

HCID 866548892-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3,5-Di(docosyloxy)benzylchloride (450 mg, 0.58 mmol), 2-hydroxy-4-methoxybenzaldehyde (185 mg, 1.22 mmol) and potassium carbonate (200 mg, 1.45 mmol) were suspended in DMF (4.5 ml), and the mixture was stirred at 80° C. for 6 hr. The reaction mixture was extracted with chloroform (20 ml), and washed 3 times with 1N hydrochloric acid (7 ml). The solvent was evaporated and the obtained residue was precipitated with methanol (5 ml) to give 2-[3′,5′-di(docosyloxy)benzyl]-4-methoxybenzaldehyde (502 g, 0.56 mmol, 97%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform (20 ml)
  2. washwashed 3 times with 1N hydrochloric acid (7 ml)
  3. customThe solvent was evaporated
  4. customthe obtained residue was precipitated with methanol (5 ml)

Sources & evidence

ORD record
ord-32940250879041589b2a3cc487d118be
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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